1-mercapto-2-phosphinobenzene | 70048-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 1-mercapto-2-phosphinobenzene
• 英文别名: o-mercaptophenylphosphine；o-Mercaptophenylphosphin；2-Phosphanylbenzenethiol
• CAS: 70048-90-7
• 化学式: C₆H₇PS
• 分子量: 142.161
• InChiKey: JOYCGVNNJGUKPI-UHFFFAOYSA-N

物化性质

• 沸点：
  74 °C(Press: 0.4 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-mercapto-2-phosphinobenzene 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 2-(trimethylsilyl)-1,3-benzothiaphosphole
  参考文献：
  名称：

  Stability and Reactivity of 1,3-Benzothiaphosphole: Metalation and Diels–Alder Chemistry

  摘要：

  The synthesis and functionalization of the parent 1,3-benzothiaphosphole is reported. The phosphole could not be isolated, but the compound could be manipulated in solution to produce several new phosphorus compounds. Metalation of the 2-position using lithium diisopropylamide proceeded smoothly according to P-31 NMR spectroscopy, and quenching with trimethysiyl chloride resulted in the desired 2-(trimethylsily1)-1,3-benzothiaphosphole. The P=C bond of the thiaphosphole was also explored as a dienophile in Diels-Alder reactions with isoprene, 2,3-dimethylbutadiene, 2,3-dibenzylbutadiene, and cyclopentadiene. The fused-ring structures were fully characterized, and a solid-state molecular structure of the 2,3-dimethylbutadiene cycloadduct was obtained. Residual dipolar coupling (RDC) NMR experiments were used to assign major and minor products for the isoprene and cyclopentadiene adducts.

  DOI：

  10.1021/acs.organomet.5b00583
• 作为产物：
  描述：

  diisopropyl (2-mercaptophenyl)phosphonate 生成 1-mercapto-2-phosphinobenzene
  参考文献：
  名称：

  用磷调谐噻吩：苯并二硫杂磷的合成和电子性质

  摘要：

  合成1,4-二巯基-2,5-二膦基苯和3,6-双（己氧基）-1,4-二巯基-2,5-二膦基苯并与各种酰氯组合得到一系列苯并双硫杂磷。已经评估了取代的苯并二硫杂磷的电化学和光物理性质，并且观察到的减少比相关的苯并硫杂磷和2,6-二苯基苯并二噻唑更容易。具有C 6 H 4 - p -CN取代基的苯并二硫杂磷在E 1/2 = −1.08 V时（相对于饱和甘汞电极（SCE））还原。已经获得了其中一些磷杂环的X射线衍射数据，并已在B3LYP水平进行了DFT计算。

  DOI：

  10.1002/chem.201402561

文献信息

• Ligation method and reagents to form an amide bond
  申请人：——

  公开号：US20040087779A1

  公开（公告）日：2004-05-06

  Methods and reagents for the formation of amide bonds between an activated carboxylic acid derivative and an azide useful in the synthesis of peptides, proteins and derivatized or labeled amino acids, peptide or proteins. The method involves the formation of a phosphinothioester which reacts with an azide resulting in amide formation. The invention provides phosphinothiol reagents which convert activated carboxylic acid derivatives to phosphinothioesters which then react with azides to form an amide bond. The methods and reagents of the invention can be used for stepwise synthesis of peptides on solid supports or for the ligation to two or more amino acids, two or more peptide or two or more protein fragments.

  本发明涉及一种在合成肽、蛋白质和衍生或标记的氨基酸、肽或蛋白质中有用的活性羧酸衍生物和叠氮化物之间形成酰胺键的方法和试剂。该方法涉及形成磷硫酰基酯，该酯与叠氮化物反应，从而形成酰胺。该发明提供了磷硫酰基硫试剂，将活性羧酸衍生物转化为磷硫酰基酯，然后与叠氮化物反应形成酰胺键。该发明的方法和试剂可用于在固相支持上逐步合成肽，或用于连接两个或更多氨基酸、两个或更多肽或两个或更多蛋白质片段。
• Process for the partial hydrogenation of fatty acid esters
  申请人：Cognis IP Management GmbH

  公开号：EP1918358A1

  公开（公告）日：2008-05-07

  Suggested is a process for the manufacture of unsaturated fatty acid alkyl esters or glycerides having a total content of C18:1 of about 30 to about 80 Mol-% by partial hydrogenation of unsaturated fatty acid esters having a total content of (C18:2+C18:3) of at least 65 Mol-% - calculated on the total amount of C18 moieties in the ester - which is characterised in that the hydrogenation is conducted in an aqueous/organic two phase system in the presence of a water soluble catalyst consisting of a Group VIII metal and a hydrophilic ligand.

  本发明提出了一种通过部分氢化不饱和脂肪酸酯来制造不饱和脂肪酸烷基酯 或甘油酯的工艺，不饱和脂肪酸烷基酯或甘油酯的 C18:1 总含量约为 30 至 80 Mol-%，不饱和脂肪酸酯的 C18:2+C18：3）至少为 65 Mol-%（按酯中 C18 分子总量计算）的不饱和脂肪酸酯进行部分氢化，其特征在于氢化是在由第八族金属和亲水配位体组成的水溶性催化剂存在下，在水/有机两相体系中进行的。
• Synthetic Tuning of Electronic and Photophysical Properties of 2-Aryl-1,3-Benzothiaphospholes
  作者：Joshua C. Worch、Danielle N. Chirdon、Andrew B. Maurer、Yunyan Qiu、Steven J. Geib、Stefan Bernhard、Kevin J. T. Noonan

  DOI：10.1021/jo400947u

  日期：2013.8.2

  A series of 2-aryl-1,3-benzothiaphospholes have been synthesized from 1-mercapto-2-phosphinobenzene and a variety of acid chlorides. The structure of 2-phenyl-1,3-benzothiaphosphole was established using X-ray diffraction. The electrochemical and photophysical properties of each benzothiaphosphole are reported and some of these molecules exhibit reversible 1-electron reductions.
• 1.3-Benzthiaphosphole
  作者：K. Issleib、R. Vollmer

  DOI：10.1016/s0040-4039(00)78720-x

  日期：1980.1
• ISSLEIB K.; VOLLMER R., TETRAHEDRON LETT., 1980, 21, NO 36, 3483-3484
  作者：ISSLEIB K.、 VOLLMER R.

  DOI：——

  日期：——